# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_111
_audit_block_doi                 10.5517/ccdc.csd.cc1ytbdh
_database_code_depnum_ccdc_archive 'CCDC 1811807'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1134/S1070328418090026 2018
loop_
_audit_author_name
_audit_author_address
xuqiwei
;Capital Normal University 
China
;
_audit_update_record             
;
2018-03-26 deposited with the CCDC.	2019-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H14 Cu2 N3 O8'
_chemical_formula_weight         539.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5272(4)
_cell_length_b                   10.6671(5)
_cell_length_c                   11.6450(5)
_cell_angle_alpha                100.8070(10)
_cell_angle_beta                 98.5420(10)
_cell_angle_gamma                115.0540(10)
_cell_volume                     1017.95(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8980
_cell_measurement_theta_min      3.025
_cell_measurement_theta_max      27.401

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.114
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             542
_exptl_absorpt_coefficient_mu    2.143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6164
_exptl_absorpt_correction_T_max  0.7984
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18268
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3582
_reflns_number_gt                2949
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0527P)²+0.8831P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3582
_refine_ls_number_parameters     297
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0966
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.64016(5) -0.17189(4) -0.13140(4) 0.01999(14) Uani 1 1 d . . .
Cu2 Cu 0.65058(5) 0.14188(4) 0.02380(4) 0.02033(14) Uani 1 1 d . . .
O1 O 0.7028(3) -0.6584(3) 0.0358(3) 0.0337(7) Uani 1 1 d D . .
O2 O 0.5872(3) -0.0662(2) -0.0029(2) 0.0189(5) Uani 1 1 d D . .
O3 O 1.1498(3) 0.0108(3) 0.1129(3) 0.0396(7) Uani 1 1 d . . .
O4 O 1.1454(3) -0.1929(3) 0.0197(3) 0.0372(7) Uani 1 1 d . . .
O5 O 0.6400(3) -0.1321(3) 0.2334(2) 0.0252(6) Uani 1 1 d . . .
O6 O 0.5147(3) -0.6419(3) 0.1210(3) 0.0397(7) Uani 1 1 d . . .
N7 N 0.7064(3) -0.2893(3) -0.2447(3) 0.0246(7) Uani 1 1 d . A .
O8 O 0.7161(3) 0.1567(3) 0.2111(2) 0.0321(6) Uani 1 1 d . . .
N9 N 0.8226(4) -0.4028(4) -0.3279(3) 0.0405(9) Uani 1 1 d U . .
N10B N 0.6669(13) -0.4795(16) -0.3919(11) 0.040(3) Uani 0.65(3) 1 d PU A 2
O7 O 0.4987(4) 0.1382(4) 0.2716(3) 0.0551(9) Uani 1 1 d . . .
C2 C 0.8638(4) -0.3559(4) 0.0813(3) 0.0234(8) Uani 1 1 d . . .
H2A H 0.9113 -0.4063 0.0433 0.028 Uiso 1 1 calc R . .
C3 C 0.9352(4) -0.2068(4) 0.1081(3) 0.0211(7) Uani 1 1 d . . .
C4 C 0.6398(4) -0.5903(4) 0.0869(3) 0.0235(8) Uani 1 1 d . . .
C5 C 0.8408(4) -0.2988(4) -0.2371(3) 0.0290(9) Uani 1 1 d . A .
H5 H 0.9347 -0.2403 -0.1763 0.035 Uiso 1 1 calc R . .
C6 C 0.8640(4) -0.1316(4) 0.1634(3) 0.0233(8) Uani 1 1 d . . .
H6 H 0.9123 -0.0316 0.1819 0.028 Uiso 1 1 calc R . .
C7 C 1.0902(4) -0.1226(4) 0.0775(3) 0.0209(7) Uani 1 1 d . . .
C1 C 0.7208(4) -0.2064(4) 0.1909(3) 0.0214(7) Uani 1 1 d . . .
C8 C 0.7208(4) -0.4297(4) 0.1114(3) 0.0225(8) Uani 1 1 d . . .
C9 C 0.6695(4) 0.0692(4) 0.3798(3) 0.0247(8) Uani 1 1 d . . .
C10 C 0.6913(4) -0.0525(4) 0.3552(3) 0.0261(8) Uani 1 1 d . . .
C11 C 0.6073(5) -0.3938(5) -0.3455(4) 0.0529(14) Uani 1 1 d . . .
H11A H 0.5064 -0.4056 -0.3801 0.063 Uiso 0.65(3) 1 calc PR A 2
H11 H 0.4964 -0.4319 -0.3629 0.063 Uiso 0.35(3) 1 calc PR A 1
C12 C 0.6493(4) -0.3530(4) 0.1656(3) 0.0243(8) Uani 1 1 d . . .
H12 H 0.5527 -0.4017 0.1847 0.029 Uiso 1 1 calc R . .
C13 C 0.9444(6) -0.4690(5) -0.4850(5) 0.0522(13) Uani 1 1 d . . .
H13A H 0.9823 -0.3747 -0.4992 0.063 Uiso 1 1 calc R A .
H13B H 0.8379 -0.5308 -0.5381 0.063 Uiso 1 1 calc R . .
C14 C 0.7459(6) -0.0991(5) 0.4469(4) 0.0439(11) Uani 1 1 d . . .
H14 H 0.7623 -0.1797 0.4289 0.053 Uiso 1 1 calc R . .
C15 C 0.6228(4) 0.1256(4) 0.2793(3) 0.0265(8) Uani 1 1 d . . .
C16 C 0.9358(5) -0.4553(5) -0.3563(4) 0.0503(13) Uani 1 1 d . A .
H16A H 0.9037 -0.5486 -0.3411 0.060 Uiso 1 1 calc R . .
H16B H 1.0414 -0.3895 -0.3033 0.060 Uiso 1 1 calc R . .
C17 C 0.7486(6) 0.0936(5) 0.5917(4) 0.0496(12) Uani 1 1 d . . .
H17 H 0.7673 0.1427 0.6718 0.060 Uiso 1 1 calc R . .
C18 C 0.6940(5) 0.1390(4) 0.4996(3) 0.0375(10) Uani 1 1 d . . .
H18 H 0.6734 0.2172 0.5179 0.045 Uiso 1 1 calc R . .
C19 C 0.7756(6) -0.0244(5) 0.5653(4) 0.0516(12) Uani 1 1 d . . .
H19 H 0.8141 -0.0538 0.6277 0.062 Uiso 1 1 calc R . .
N10A N 0.680(3) -0.436(3) -0.416(2) 0.040(3) Uani 0.35(3) 1 d PU A 1
H2 H 0.616(5) -0.075(5) 0.064(2) 0.037(13) Uiso 1 1 d D . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O6 1.949(2) 2_645 ?
Cu1 O3 1.955(2) 2_755 ?
Cu1 O2 1.959(2) . ?
Cu1 N7 2.001(3) . ?
Cu1 O7 2.128(3) 2_655 ?
Cu2 O1 1.944(2) 1_565 ?
Cu2 O4 1.957(2) 2_755 ?
Cu2 O2 1.984(2) . ?
Cu2 O2 2.014(2) 2_655 ?
Cu2 O8 2.135(2) . ?
Cu2 Cu2 3.0405(8) 2_655 ?
O1 C4 1.246(4) . ?
O1 Cu2 1.944(2) 1_545 ?
O2 Cu2 2.014(2) 2_655 ?
O2 H2 0.826(19) . ?
O3 C7 1.242(4) . ?
O3 Cu1 1.955(2) 2_755 ?
O4 C7 1.242(4) . ?
O4 Cu2 1.957(2) 2_755 ?
O5 C1 1.396(4) . ?
O5 C10 1.401(4) . ?
O6 C4 1.244(4) . ?
O6 Cu1 1.949(2) 2_645 ?
N7 C5 1.318(5) . ?
N7 C11 1.342(5) . ?
O8 C15 1.260(4) . ?
N9 C5 1.312(5) . ?
N9 N10B 1.357(11) . ?
N9 N10A 1.43(2) . ?
N9 C16 1.461(5) . ?
N10B C11 1.340(12) . ?
O7 C15 1.237(5) . ?
O7 Cu1 2.128(3) 2_655 ?
C2 C3 1.387(5) . ?
C2 C8 1.392(5) . ?
C2 H2A 0.9300 . ?
C3 C6 1.384(5) . ?
C3 C7 1.506(4) . ?
C4 C8 1.498(5) . ?
C5 H5 0.9300 . ?
C6 C1 1.380(5) . ?
C6 H6 0.9300 . ?
C1 C12 1.365(5) . ?
C8 C12 1.392(5) . ?
C9 C10 1.385(5) . ?
C9 C18 1.386(5) . ?
C9 C15 1.505(5) . ?
C10 C14 1.382(5) . ?
C11 N10A 1.29(2) . ?
C11 H11A 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C16 1.496(7) . ?
C13 C13 1.516(8) 2_744 ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C19 1.378(6) . ?
C14 H14 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C19 1.377(6) . ?
C17 C18 1.378(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Cu1 O3 157.85(13) 2_645 2_755 ?
O6 Cu1 O2 92.50(10) 2_645 . ?
O3 Cu1 O2 94.40(10) 2_755 . ?
O6 Cu1 N7 84.37(11) 2_645 . ?
O3 Cu1 N7 85.96(11) 2_755 . ?
O2 Cu1 N7 172.00(11) . . ?
O6 Cu1 O7 101.09(14) 2_645 2_655 ?
O3 Cu1 O7 99.48(14) 2_755 2_655 ?
O2 Cu1 O7 93.37(11) . 2_655 ?
N7 Cu1 O7 94.45(12) . 2_655 ?
O1 Cu2 O4 84.38(10) 1_565 2_755 ?
O1 Cu2 O2 175.13(11) 1_565 . ?
O4 Cu2 O2 95.80(10) 2_755 . ?
O1 Cu2 O2 97.10(10) 1_565 2_655 ?
O4 Cu2 O2 159.18(11) 2_755 2_655 ?
O2 Cu2 O2 81.01(10) . 2_655 ?
O1 Cu2 O8 99.63(11) 1_565 . ?
O4 Cu2 O8 102.03(11) 2_755 . ?
O2 Cu2 O8 85.11(10) . . ?
O2 Cu2 O8 98.20(10) 2_655 . ?
O1 Cu2 Cu2 137.07(8) 1_565 2_655 ?
O4 Cu2 Cu2 133.25(8) 2_755 2_655 ?
O2 Cu2 Cu2 40.87(7) . 2_655 ?
O2 Cu2 Cu2 40.14(6) 2_655 2_655 ?
O8 Cu2 Cu2 92.23(7) . 2_655 ?
C4 O1 Cu2 126.2(2) . 1_545 ?
Cu1 O2 Cu2 121.84(11) . . ?
Cu1 O2 Cu2 112.98(11) . 2_655 ?
Cu2 O2 Cu2 98.99(10) . 2_655 ?
Cu1 O2 H2 113(3) . . ?
Cu2 O2 H2 105(3) . . ?
Cu2 O2 H2 102(3) 2_655 . ?
C7 O3 Cu1 135.1(2) . 2_755 ?
C7 O4 Cu2 133.8(2) . 2_755 ?
C1 O5 C10 119.0(3) . . ?
C4 O6 Cu1 138.7(2) . 2_645 ?
C5 N7 C11 103.2(3) . . ?
C5 N7 Cu1 131.9(2) . . ?
C11 N7 Cu1 124.5(3) . . ?
C15 O8 Cu2 126.4(2) . . ?
C5 N9 N10B 110.6(5) . . ?
C5 N9 N10A 106.4(9) . . ?
N10B N9 N10A 23.0(7) . . ?
C5 N9 C16 130.0(4) . . ?
N10B N9 C16 118.8(6) . . ?
N10A N9 C16 122.0(9) . . ?
C11 N10B N9 100.6(7) . . ?
C15 O7 Cu1 131.8(3) . 2_655 ?
C3 C2 C8 119.7(3) . . ?
C3 C2 H2A 120.2 . . ?
C8 C2 H2A 120.2 . . ?
C6 C3 C2 120.3(3) . . ?
C6 C3 C7 118.2(3) . . ?
C2 C3 C7 121.4(3) . . ?
O6 C4 O1 126.7(3) . . ?
O6 C4 C8 115.3(3) . . ?
O1 C4 C8 118.0(3) . . ?
N9 C5 N7 110.1(3) . . ?
N9 C5 H5 125.0 . . ?
N7 C5 H5 125.0 . . ?
C1 C6 C3 119.4(3) . . ?
C1 C6 H6 120.3 . . ?
C3 C6 H6 120.3 . . ?
O3 C7 O4 126.6(3) . . ?
O3 C7 C3 116.4(3) . . ?
O4 C7 C3 117.0(3) . . ?
C12 C1 C6 121.0(3) . . ?
C12 C1 O5 119.5(3) . . ?
C6 C1 O5 119.1(3) . . ?
C12 C8 C2 119.5(3) . . ?
C12 C8 C4 118.5(3) . . ?
C2 C8 C4 122.1(3) . . ?
C10 C9 C18 118.2(3) . . ?
C10 C9 C15 120.9(3) . . ?
C18 C9 C15 120.8(3) . . ?
C14 C10 C9 121.5(4) . . ?
C14 C10 O5 122.4(3) . . ?
C9 C10 O5 115.8(3) . . ?
N10A C11 N10B 24.6(8) . . ?
N10A C11 N7 113.7(10) . . ?
N10B C11 N7 113.9(6) . . ?
N10A C11 H11A 117.7 . . ?
N10B C11 H11A 123.0 . . ?
N7 C11 H11A 123.0 . . ?
N10A C11 H11 123.2 . . ?
N10B C11 H11 117.4 . . ?
N7 C11 H11 123.2 . . ?
H11A C11 H11 22.5 . . ?
C1 C12 C8 120.1(3) . . ?
C1 C12 H12 120.0 . . ?
C8 C12 H12 120.0 . . ?
C16 C13 C13 111.8(6) . 2_744 ?
C16 C13 H13A 109.3 . . ?
C13 C13 H13A 109.3 2_744 . ?
C16 C13 H13B 109.3 . . ?
C13 C13 H13B 109.3 2_744 . ?
H13A C13 H13B 107.9 . . ?
C19 C14 C10 119.1(4) . . ?
C19 C14 H14 120.5 . . ?
C10 C14 H14 120.5 . . ?
O7 C15 O8 126.3(3) . . ?
O7 C15 C9 117.7(3) . . ?
O8 C15 C9 116.1(3) . . ?
N9 C16 C13 112.3(4) . . ?
N9 C16 H16A 109.1 . . ?
C13 C16 H16A 109.1 . . ?
N9 C16 H16B 109.1 . . ?
C13 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
C19 C17 C18 120.1(4) . . ?
C19 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C9 120.7(4) . . ?
C17 C18 H18 119.7 . . ?
C9 C18 H18 119.7 . . ?
C17 C19 C14 120.3(4) . . ?
C17 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C11 N10A N9 99.1(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 Cu1 O2 Cu2 -164.00(15) 2_645 . . . ?
O3 Cu1 O2 Cu2 37.06(16) 2_755 . . . ?
N7 Cu1 O2 Cu2 129.3(7) . . . . ?
O7 Cu1 O2 Cu2 -62.73(16) 2_655 . . . ?
O6 Cu1 O2 Cu2 -46.41(14) 2_645 . . 2_655 ?
O3 Cu1 O2 Cu2 154.65(14) 2_755 . . 2_655 ?
N7 Cu1 O2 Cu2 -113.1(7) . . . 2_655 ?
O7 Cu1 O2 Cu2 54.86(14) 2_655 . . 2_655 ?
O1 Cu2 O2 Cu1 56.8(11) 1_565 . . . ?
O4 Cu2 O2 Cu1 -34.95(16) 2_755 . . . ?
O2 Cu2 O2 Cu1 124.30(19) 2_655 . . . ?
O8 Cu2 O2 Cu1 -136.58(15) . . . . ?
Cu2 Cu2 O2 Cu1 124.30(19) 2_655 . . . ?
O1 Cu2 O2 Cu2 -67.4(11) 1_565 . . 2_655 ?
O4 Cu2 O2 Cu2 -159.25(12) 2_755 . . 2_655 ?
O2 Cu2 O2 Cu2 0.0 2_655 . . 2_655 ?
O8 Cu2 O2 Cu2 99.12(11) . . . 2_655 ?
O6 Cu1 N7 C5 -114.9(3) 2_645 . . . ?
O3 Cu1 N7 C5 45.1(3) 2_755 . . . ?
O2 Cu1 N7 C5 -47.7(9) . . . . ?
O7 Cu1 N7 C5 144.3(3) 2_655 . . . ?
O6 Cu1 N7 C11 56.7(4) 2_645 . . . ?
O3 Cu1 N7 C11 -143.2(4) 2_755 . . . ?
O2 Cu1 N7 C11 124.0(7) . . . . ?
O7 Cu1 N7 C11 -44.0(4) 2_655 . . . ?
O1 Cu2 O8 C15 98.0(3) 1_565 . . . ?
O4 Cu2 O8 C15 -175.7(3) 2_755 . . . ?
O2 Cu2 O8 C15 -80.8(3) . . . . ?
O2 Cu2 O8 C15 -0.6(3) 2_655 . . . ?
Cu2 Cu2 O8 C15 -40.5(3) 2_655 . . . ?
C5 N9 N10B C11 11.9(13) . . . . ?
N10A N9 N10B C11 -72(3) . . . . ?
C16 N9 N10B C11 -176.3(7) . . . . ?
C8 C2 C3 C6 -0.7(5) . . . . ?
C8 C2 C3 C7 179.8(3) . . . . ?
Cu1 O6 C4 O1 5.2(7) 2_645 . . . ?
Cu1 O6 C4 C8 -174.5(3) 2_645 . . . ?
Cu2 O1 C4 O6 -13.5(6) 1_545 . . . ?
Cu2 O1 C4 C8 166.2(2) 1_545 . . . ?
N10B N9 C5 N7 -7.8(10) . . . . ?
N10A N9 C5 N7 16.1(12) . . . . ?
C16 N9 C5 N7 -178.5(4) . . . . ?
C11 N7 C5 N9 -0.1(5) . . . . ?
Cu1 N7 C5 N9 172.9(3) . . . . ?
C2 C3 C6 C1 -0.4(5) . . . . ?
C7 C3 C6 C1 179.1(3) . . . . ?
Cu1 O3 C7 O4 -15.3(6) 2_755 . . . ?
Cu1 O3 C7 C3 164.8(3) 2_755 . . . ?
Cu2 O4 C7 O3 9.7(6) 2_755 . . . ?
Cu2 O4 C7 C3 -170.4(2) 2_755 . . . ?
C6 C3 C7 O3 5.3(5) . . . . ?
C2 C3 C7 O3 -175.2(3) . . . . ?
C6 C3 C7 O4 -174.6(3) . . . . ?
C2 C3 C7 O4 4.9(5) . . . . ?
C3 C6 C1 C12 0.7(5) . . . . ?
C3 C6 C1 O5 -172.5(3) . . . . ?
C10 O5 C1 C12 107.0(4) . . . . ?
C10 O5 C1 C6 -79.7(4) . . . . ?
C3 C2 C8 C12 1.5(5) . . . . ?
C3 C2 C8 C4 -178.8(3) . . . . ?
O6 C4 C8 C12 -1.9(5) . . . . ?
O1 C4 C8 C12 178.4(3) . . . . ?
O6 C4 C8 C2 178.4(3) . . . . ?
O1 C4 C8 C2 -1.3(5) . . . . ?
C18 C9 C10 C14 -4.0(6) . . . . ?
C15 C9 C10 C14 175.0(4) . . . . ?
C18 C9 C10 O5 169.9(3) . . . . ?
C15 C9 C10 O5 -11.0(5) . . . . ?
C1 O5 C10 C14 -37.3(5) . . . . ?
C1 O5 C10 C9 148.7(3) . . . . ?
N9 N10B C11 N10A 83(3) . . . . ?
N9 N10B C11 N7 -12.4(14) . . . . ?
C5 N7 C11 N10A -18.6(15) . . . . ?
Cu1 N7 C11 N10A 167.7(14) . . . . ?
C5 N7 C11 N10B 8.3(10) . . . . ?
Cu1 N7 C11 N10B -165.4(9) . . . . ?
C6 C1 C12 C8 0.1(5) . . . . ?
O5 C1 C12 C8 173.3(3) . . . . ?
C2 C8 C12 C1 -1.2(5) . . . . ?
C4 C8 C12 C1 179.1(3) . . . . ?
C9 C10 C14 C19 1.5(6) . . . . ?
O5 C10 C14 C19 -172.1(4) . . . . ?
Cu1 O7 C15 O8 14.2(6) 2_655 . . . ?
Cu1 O7 C15 C9 -166.3(3) 2_655 . . . ?
Cu2 O8 C15 O7 -31.8(5) . . . . ?
Cu2 O8 C15 C9 148.7(2) . . . . ?
C10 C9 C15 O7 123.0(4) . . . . ?
C18 C9 C15 O7 -58.0(5) . . . . ?
C10 C9 C15 O8 -57.5(5) . . . . ?
C18 C9 C15 O8 121.5(4) . . . . ?
C5 N9 C16 C13 -131.1(5) . . . . ?
N10B N9 C16 C13 58.9(11) . . . . ?
N10A N9 C16 C13 32.3(14) . . . . ?
C13 C13 C16 N9 -177.0(5) 2_744 . . . ?
C19 C17 C18 C9 -1.7(7) . . . . ?
C10 C9 C18 C17 4.1(6) . . . . ?
C15 C9 C18 C17 -175.0(4) . . . . ?
C18 C17 C19 C14 -1.0(8) . . . . ?
C10 C14 C19 C17 1.1(7) . . . . ?
N10B C11 N10A N9 -69(3) . . . . ?
N7 C11 N10A N9 26.9(18) . . . . ?
C5 N9 N10A C11 -25.3(17) . . . . ?
N10B N9 N10A C11 79(3) . . . . ?
C16 N9 N10A C11 167.9(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.191
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.090
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_111_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1832426'
loop_
_audit_author_name
_audit_author_address
xuqiwei
;Capital Normal University 
China
;
_audit_update_record             
;
2018-03-26 deposited with the CCDC.	2019-05-14 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_audit_creation_date             2016-05-29
_chemical_formula_sum            'C60 H46 N6 Ni3 O18'
_chemical_formula_weight         1315.160
_refine_ls_R_factor_all          0.127
_cell_length_a                   8.034(2)
_cell_length_b                   9.981(2)
_cell_length_c                   18.072(4)
_cell_angle_alpha                87.730(8)
_cell_angle_beta                 83.662(8)
_cell_angle_gamma                76.257(8)
_cell_volume                     1398.9(5)
_cell_formula_units_Z            1
_symmetry_int_tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  -P_1

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
Ni ? 1.200
O ? 1.200
H ? 1.200
N ? 1.200
C ? 1.200


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
Ni1 Ni 0.1022(1) 0.5385(1) 0.5439(0) 1.000 2 i ? d Uani 0.0225(2)
Ni2 Ni 0.0000 0.0000 1.0000 1.000 1 a ? d Uani 0.0218(2)
O7 O 0.0017(4) 0.4049(3) 0.6113(2) 1.000 2 i ? d Uani 0.0374(9)
O3 O -0.2465(4) -0.1113(3) 0.6662(2) 1.000 2 i ? d Uani 0.0305(8)
O4 O 0.0069(4) -0.0036(3) 0.8865(2) 1.000 2 i ? d Uani 0.0274(8)
O6 O -0.1678(4) 0.3368(3) 0.5393(2) 1.000 2 i ? d Uani 0.0349(9)
O1 O -0.2812(4) -0.3796(3) 0.5012(2) 1.000 2 i ? d Uani 0.0345(9)
O5 O 0.1059(5) 0.1833(4) 0.8559(2) 1.000 2 i ? d Uani 0.0592(12)
O8 O 0.1982(4) 0.1036(3) 0.9906(2) 1.000 2 i ? d Uani 0.0333(9)
H8A H 0.1919 0.1554 0.9513 1.000 2 i ? d Uiso 0.05000
H8B H 0.2967 0.0452 0.9870 1.000 2 i ? d Uiso 0.05000
O2 O -0.1086(4) -0.3132(3) 0.5713(2) 1.000 2 i ? d Uani 0.0411(9)
N2 N 0.7244(6) 0.7500(5) 0.8947(2) 1.000 2 i ? d Uani 0.0472(12)
N1 N 0.2418(5) 0.5811(4) 0.6219(2) 1.000 2 i ? d Uani 0.0238(9)
N3 N 0.1840(5) -0.1847(4) 0.9987(2) 1.000 2 i ? d Uani 0.0272(10)
C1 C -0.2527(6) -0.2998(5) 0.5477(2) 1.000 2 i ? d Uani 0.0238(11)
C5 C -0.6803(6) 0.0316(5) 0.6153(3) 1.000 2 i ? d Uani 0.0413(14)
H5 H -0.7729 0.1057 0.6276 1.000 2 i ? calc Uiso 0.05000
C2 C -0.3989(6) -0.1845(4) 0.5739(2) 1.000 2 i ? d Uani 0.0214(11)
C14 C -0.0930(6) 0.3278(5) 0.5973(3) 1.000 2 i ? d Uani 0.0245(12)
C4 C -0.6925(6) -0.0619(5) 0.5632(3) 1.000 2 i ? d Uani 0.0397(14)
H4 H -0.7951 -0.0537 0.5422 1.000 2 i ? calc Uiso 0.04800
C3 C -0.5538(6) -0.1663(5) 0.5425(2) 1.000 2 i ? d Uani 0.0295(12)
H3 H -0.5626 -0.2273 0.5064 1.000 2 i ? calc Uiso 0.03500
C6 C -0.5318(6) 0.0154(5) 0.6491(3) 1.000 2 i ? d Uani 0.0344(13)
H6 H -0.5257 0.0761 0.6859 1.000 2 i ? calc Uiso 0.04100
C7 C -0.3917(6) -0.0910(5) 0.6285(2) 1.000 2 i ? d Uani 0.0238(11)
C8 C -0.1899(6) 0.0032(5) 0.6839(2) 1.000 2 i ? d Uani 0.0239(11)
C9 C -0.1872(6) 0.1131(5) 0.6347(2) 1.000 2 i ? d Uani 0.0260(12)
H9 H -0.2330 0.1158 0.5894 1.000 2 i ? calc Uiso 0.03100
C10 C -0.1158(5) 0.2189(5) 0.6536(2) 1.000 2 i ? d Uani 0.0200(11)
C11 C -0.0483(6) 0.2138(5) 0.7211(2) 1.000 2 i ? d Uani 0.0233(11)
H11 H -0.0012 0.2852 0.7340 1.000 2 i ? calc Uiso 0.02800
C12 C -0.0502(6) 0.1036(5) 0.7697(2) 1.000 2 i ? d Uani 0.0233(11)
C13 C -0.1236(6) -0.0013(5) 0.7508(2) 1.000 2 i ? d Uani 0.0246(11)
H13 H -0.1278 -0.0747 0.7837 1.000 2 i ? calc Uiso 0.03000
C15 C 0.0275(6) 0.0931(5) 0.8430(3) 1.000 2 i ? d Uani 0.0289(12)
C20 C 0.3114(6) -0.2051(5) 1.0421(3) 1.000 2 i ? d Uani 0.0372(14)
H20 H 0.3173 -0.1332 1.0721 1.000 2 i ? calc Uiso 0.04500
C19 C 0.4342(6) -0.3258(5) 1.0451(3) 1.000 2 i ? d Uani 0.0373(14)
H19 H 0.5186 -0.3349 1.0774 1.000 2 i ? calc Uiso 0.04500
C18 C 0.4331(6) -0.4344(4) 1.0001(3) 1.000 2 i ? d Uani 0.0263(12)
C17 C 0.3015(6) -0.4130(5) 0.9546(3) 1.000 2 i ? d Uani 0.0361(13)
H17 H 0.2943 -0.4824 0.9231 1.000 2 i ? calc Uiso 0.04300
C16 C 0.1812(6) -0.2891(5) 0.9557(3) 1.000 2 i ? d Uani 0.0351(13)
H16 H 0.0934 -0.2779 0.9249 1.000 2 i ? calc Uiso 0.04200
C28 C 0.5788(8) 0.8341(6) 0.8767(3) 1.000 2 i ? d Uani 0.0450(15)
H28 H 0.5404 0.9174 0.9014 1.000 2 i ? calc Uiso 0.05400
C27 C 0.4820(7) 0.8060(5) 0.8242(3) 1.000 2 i ? d Uani 0.0392(14)
H27 H 0.3817 0.8695 0.8141 1.000 2 i ? calc Uiso 0.04700
C26 C 0.5335(6) 0.6831(5) 0.7860(3) 1.000 2 i ? d Uani 0.0304(12)
C30 C 0.6861(7) 0.5954(6) 0.8049(3) 1.000 2 i ? d Uani 0.0481(16)
H30 H 0.7279 0.5112 0.7811 1.000 2 i ? calc Uiso 0.05800
C29 C 0.7748(7) 0.6324(7) 0.8582(3) 1.000 2 i ? d Uani 0.0572(17)
H29 H 0.8761 0.5715 0.8694 1.000 2 i ? calc Uiso 0.06900
C23 C 0.4315(6) 0.6461(5) 0.7302(3) 1.000 2 i ? d Uani 0.0289(12)
C22 C 0.2587(6) 0.7070(5) 0.7291(3) 1.000 2 i ? d Uani 0.0397(14)
H22 H 0.2029 0.7712 0.7649 1.000 2 i ? calc Uiso 0.04800
C21 C 0.1686(6) 0.6729(5) 0.6749(3) 1.000 2 i ? d Uani 0.0366(14)
H21 H 0.0522 0.7154 0.6752 1.000 2 i ? calc Uiso 0.04400
C25 C 0.4067(6) 0.5212(5) 0.6230(3) 1.000 2 i ? d Uani 0.0306(12)
H25 H 0.4591 0.4570 0.5866 1.000 2 i ? calc Uiso 0.03700
C24 C 0.5047(6) 0.5492(5) 0.6757(3) 1.000 2 i ? d Uani 0.0352(13)
H24 H 0.6201 0.5033 0.6747 1.000 2 i ? calc Uiso 0.04200
O9 O 0.2742(13) 0.3779(9) 0.8116(5) 1.000 2 i ? d Uani 0.217(4)
H9A H 0.2930 0.2905 0.8117 1.000 2 i ? d Uiso 0.32600
H9B H 0.1718 0.4125 0.8015 1.000 2 i ? d Uiso 0.32600



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 O2 . 1_565 1.997(3) no
Ni1 O1 . 2_556 2.001(3) no
Ni1 N1 . . 2.012(3) no
Ni1 O6 . 2_566 2.019(3) no
Ni1 O7 . . 2.019(3) no
Ni1 Ni1 . 2_566 2.6598(11) no
Ni2 O4 . 2_557 2.048(3) no
Ni2 O4 . . 2.048(3) no
Ni2 N3 . 2_557 2.070(4) no
Ni2 N3 . . 2.070(4) no
Ni2 O8 . . 2.084(3) no
Ni2 O8 . 2_557 2.084(3) no
O7 C14 . . 1.254(5) no
O3 C7 . . 1.385(5) no
O3 C8 . . 1.387(5) no
O4 C15 . . 1.250(5) no
O6 C14 . . 1.255(5) no
O6 Ni1 . 2_566 2.019(3) no
O1 C1 . . 1.256(5) no
O1 Ni1 . 2_556 2.001(3) no
O5 C15 . . 1.257(5) no
O8 H8A . . 0.8608 no
O8 H8B . . 0.8611 no
O2 C1 . . 1.253(5) no
O2 Ni1 . 1_545 1.997(3) no
N2 C29 . . 1.324(7) no
N2 C28 . . 1.332(6) no
N1 C25 . . 1.320(5) no
N1 C21 . . 1.339(5) no
N3 C16 . . 1.330(5) no
N3 C20 . . 1.331(5) no
C1 C2 . . 1.486(6) no
C5 C6 . . 1.373(6) no
C5 C4 . . 1.379(6) no
C5 H5 . . 0.9300 no
C2 C3 . . 1.394(6) no
C2 C7 . . 1.399(6) no
C14 C10 . . 1.488(6) no
C4 C3 . . 1.362(6) no
C4 H4 . . 0.9300 no
C3 H3 . . 0.9300 no
C6 C7 . . 1.380(6) no
C6 H6 . . 0.9300 no
C8 C13 . . 1.369(6) no
C8 C9 . . 1.388(6) no
C9 C10 . . 1.385(6) no
C9 H9 . . 0.9300 no
C10 C11 . . 1.385(5) no
C11 C12 . . 1.381(6) no
C11 H11 . . 0.9300 no
C12 C13 . . 1.388(6) no
C12 C15 . . 1.515(6) no
C13 H13 . . 0.9300 no
C20 C19 . . 1.367(6) no
C20 H20 . . 0.9300 no
C19 C18 . . 1.383(6) no
C19 H19 . . 0.9300 no
C18 C17 . . 1.382(6) no
C18 C18 . 2_647 1.483(8) no
C17 C16 . . 1.376(6) no
C17 H17 . . 0.9300 no
C16 H16 . . 0.9300 no
C28 C27 . . 1.368(6) no
C28 H28 . . 0.9300 no
C27 C26 . . 1.383(6) no
C27 H27 . . 0.9300 no
C26 C30 . . 1.394(6) no
C26 C23 . . 1.477(6) no
C30 C29 . . 1.371(7) no
C30 H30 . . 0.9300 no
C29 H29 . . 0.9300 no
C23 C22 . . 1.379(6) no
C23 C24 . . 1.390(6) no
C22 C21 . . 1.378(6) no
C22 H22 . . 0.9300 no
C21 H21 . . 0.9300 no
C25 C24 . . 1.376(6) no
C25 H25 . . 0.9300 no
C24 H24 . . 0.9300 no
O9 H9A . . 0.8499 no
O9 H9B . . 0.8499 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 Ni1 O1 1_565 . 2_556 166.76(12) no
O2 Ni1 N1 1_565 . . 96.60(14) no
O1 Ni1 N1 2_556 . . 96.64(14) no
O2 Ni1 O6 1_565 . 2_566 88.04(14) no
O1 Ni1 O6 2_556 . 2_566 89.95(13) no
N1 Ni1 O6 . . 2_566 99.51(14) no
O2 Ni1 O7 1_565 . . 89.68(14) no
O1 Ni1 O7 2_556 . . 89.43(14) no
N1 Ni1 O7 . . . 93.10(14) no
O6 Ni1 O7 2_566 . . 167.36(12) no
O2 Ni1 Ni1 1_565 . 2_566 82.53(9) no
O1 Ni1 Ni1 2_556 . 2_566 84.34(9) no
N1 Ni1 Ni1 . . 2_566 171.79(11) no
O6 Ni1 Ni1 2_566 . 2_566 88.63(9) no
O7 Ni1 Ni1 . . 2_566 78.75(9) no
O4 Ni2 O4 2_557 . . 180.0() no
O4 Ni2 N3 2_557 . 2_557 90.35(13) no
O4 Ni2 N3 . . 2_557 89.65(13) no
O4 Ni2 N3 2_557 . . 89.65(13) no
O4 Ni2 N3 . . . 90.35(13) no
N3 Ni2 N3 2_557 . . 180.0(2) no
O4 Ni2 O8 2_557 . . 89.40(12) no
O4 Ni2 O8 . . . 90.60(12) no
N3 Ni2 O8 2_557 . . 91.29(14) no
N3 Ni2 O8 . . . 88.71(14) no
O4 Ni2 O8 2_557 . 2_557 90.60(12) no
O4 Ni2 O8 . . 2_557 89.40(12) no
N3 Ni2 O8 2_557 . 2_557 88.71(14) no
N3 Ni2 O8 . . 2_557 91.29(14) no
O8 Ni2 O8 . . 2_557 180.00(13) no
C14 O7 Ni1 . . . 129.7(3) no
C7 O3 C8 . . . 118.4(3) no
C15 O4 Ni2 . . . 125.3(3) no
C14 O6 Ni1 . . 2_566 117.9(3) no
C1 O1 Ni1 . . 2_556 123.8(3) no
Ni2 O8 H8A . . . 109.60 no
Ni2 O8 H8B . . . 110.10 no
H8A O8 H8B . . . 108.70 no
C1 O2 Ni1 . . 1_545 126.3(3) no
C29 N2 C28 . . . 116.0(5) no
C25 N1 C21 . . . 117.6(4) no
C25 N1 Ni1 . . . 122.1(3) no
C21 N1 Ni1 . . . 120.3(3) no
C16 N3 C20 . . . 116.4(4) no
C16 N3 Ni2 . . . 122.6(3) no
C20 N3 Ni2 . . . 121.0(3) no
O2 C1 O1 . . . 122.9(4) no
O2 C1 C2 . . . 120.2(4) no
O1 C1 C2 . . . 116.9(4) no
C6 C5 C4 . . . 120.1(5) no
C6 C5 H5 . . . 120.00 no
C4 C5 H5 . . . 120.00 no
C3 C2 C7 . . . 117.1(4) no
C3 C2 C1 . . . 118.8(4) no
C7 C2 C1 . . . 124.1(4) no
O7 C14 O6 . . . 124.2(4) no
O7 C14 C10 . . . 117.0(4) no
O6 C14 C10 . . . 118.8(4) no
C3 C4 C5 . . . 119.8(5) no
C3 C4 H4 . . . 120.10 no
C5 C4 H4 . . . 120.10 no
C4 C3 C2 . . . 122.0(4) no
C4 C3 H3 . . . 119.00 no
C2 C3 H3 . . . 119.00 no
C5 C6 C7 . . . 120.0(4) no
C5 C6 H6 . . . 120.00 no
C7 C6 H6 . . . 120.00 no
C6 C7 O3 . . . 119.4(4) no
C6 C7 C2 . . . 120.9(4) no
O3 C7 C2 . . . 119.5(4) no
C13 C8 O3 . . . 116.6(4) no
C13 C8 C9 . . . 120.7(4) no
O3 C8 C9 . . . 122.5(4) no
C10 C9 C8 . . . 119.4(4) no
C10 C9 H9 . . . 120.30 no
C8 C9 H9 . . . 120.30 no
C11 C10 C9 . . . 119.7(4) no
C11 C10 C14 . . . 120.3(4) no
C9 C10 C14 . . . 119.5(4) no
C12 C11 C10 . . . 120.6(4) no
C12 C11 H11 . . . 119.70 no
C10 C11 H11 . . . 119.70 no
C11 C12 C13 . . . 119.4(4) no
C11 C12 C15 . . . 121.8(4) no
C13 C12 C15 . . . 118.8(4) no
C8 C13 C12 . . . 120.1(4) no
C8 C13 H13 . . . 119.90 no
C12 C13 H13 . . . 119.90 no
O4 C15 O5 . . . 124.9(4) no
O4 C15 C12 . . . 117.5(4) no
O5 C15 C12 . . . 117.5(4) no
N3 C20 C19 . . . 123.7(4) no
N3 C20 H20 . . . 118.10 no
C19 C20 H20 . . . 118.10 no
C20 C19 C18 . . . 120.2(4) no
C20 C19 H19 . . . 119.90 no
C18 C19 H19 . . . 119.90 no
C17 C18 C19 . . . 116.1(4) no
C17 C18 C18 . . 2_647 122.0(5) no
C19 C18 C18 . . 2_647 121.9(5) no
C16 C17 C18 . . . 120.2(4) no
C16 C17 H17 . . . 119.90 no
C18 C17 H17 . . . 119.90 no
N3 C16 C17 . . . 123.4(4) no
N3 C16 H16 . . . 118.30 no
C17 C16 H16 . . . 118.30 no
N2 C28 C27 . . . 124.4(5) no
N2 C28 H28 . . . 117.80 no
C27 C28 H28 . . . 117.80 no
C28 C27 C26 . . . 119.9(5) no
C28 C27 H27 . . . 120.00 no
C26 C27 H27 . . . 120.00 no
C27 C26 C30 . . . 115.6(5) no
C27 C26 C23 . . . 122.1(5) no
C30 C26 C23 . . . 122.3(5) no
C29 C30 C26 . . . 120.4(5) no
C29 C30 H30 . . . 119.80 no
C26 C30 H30 . . . 119.80 no
N2 C29 C30 . . . 123.7(6) no
N2 C29 H29 . . . 118.10 no
C30 C29 H29 . . . 118.10 no
C22 C23 C24 . . . 116.4(4) no
C22 C23 C26 . . . 121.7(4) no
C24 C23 C26 . . . 121.8(4) no
C21 C22 C23 . . . 120.2(5) no
C21 C22 H22 . . . 119.90 no
C23 C22 H22 . . . 119.90 no
N1 C21 C22 . . . 122.7(4) no
N1 C21 H21 . . . 118.70 no
C22 C21 H21 . . . 118.70 no
N1 C25 C24 . . . 123.1(4) no
N1 C25 H25 . . . 118.50 no
C24 C25 H25 . . . 118.50 no
C25 C24 C23 . . . 120.1(4) no
C25 C24 H24 . . . 120.00 no
C23 C24 H24 . . . 120.00 no
H9A O9 H9B . . . 109.50 no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 Ni1 O7 C14 1_565 . . . 89.0(4) no
O1 Ni1 O7 C14 2_556 . . . -77.8(4) no
N1 Ni1 O7 C14 . . . . -174.4(4) no
O6 Ni1 O7 C14 2_566 . . . 9.4(9) no
Ni1 Ni1 O7 C14 2_566 . . . 6.6(4) no
O4 Ni2 O4 C15 2_557 . . . -172.(100) no
N3 Ni2 O4 C15 2_557 . . . 51.6(4) no
N3 Ni2 O4 C15 . . . . -128.4(4) no
O8 Ni2 O4 C15 . . . . -39.7(4) no
O8 Ni2 O4 C15 2_557 . . . 140.3(4) no
O2 Ni1 N1 C25 1_565 . . . -171.6(4) no
O1 Ni1 N1 C25 2_556 . . . 8.6(4) no
O6 Ni1 N1 C25 2_566 . . . -82.5(4) no
O7 Ni1 N1 C25 . . . . 98.4(4) no
Ni1 Ni1 N1 C25 2_566 . . . 105.0(8) no
O2 Ni1 N1 C21 1_565 . . . 8.3(4) no
O1 Ni1 N1 C21 2_556 . . . -171.5(4) no
O6 Ni1 N1 C21 2_566 . . . 97.4(4) no
O7 Ni1 N1 C21 . . . . -81.7(4) no
Ni1 Ni1 N1 C21 2_566 . . . -75.1(9) no
O4 Ni2 N3 C16 2_557 . . . 138.2(4) no
O4 Ni2 N3 C16 . . . . -41.8(4) no
N3 Ni2 N3 C16 2_557 . . . 44.(4) no
O8 Ni2 N3 C16 . . . . -132.4(4) no
O8 Ni2 N3 C16 2_557 . . . 47.6(4) no
O4 Ni2 N3 C20 2_557 . . . -41.1(4) no
O4 Ni2 N3 C20 . . . . 138.9(4) no
N3 Ni2 N3 C20 2_557 . . . -135.(4) no
O8 Ni2 N3 C20 . . . . 48.3(4) no
O8 Ni2 N3 C20 2_557 . . . -131.7(4) no
Ni1 O2 C1 O1 1_545 . . . -1.6(7) no
Ni1 O2 C1 C2 1_545 . . . 179.2(3) no
Ni1 O1 C1 O2 2_556 . . . -0.9(6) no
Ni1 O1 C1 C2 2_556 . . . 178.3(3) no
O2 C1 C2 C3 . . . . 175.2(4) no
O1 C1 C2 C3 . . . . -4.0(6) no
O2 C1 C2 C7 . . . . -4.4(7) no
O1 C1 C2 C7 . . . . 176.4(4) no
Ni1 O7 C14 O6 . . . . -12.6(7) no
Ni1 O7 C14 C10 . . . . 167.1(3) no
Ni1 O6 C14 O7 2_566 . . . 10.3(6) no
Ni1 O6 C14 C10 2_566 . . . -169.3(3) no
C6 C5 C4 C3 . . . . -3.4(8) no
C5 C4 C3 C2 . . . . 1.6(7) no
C7 C2 C3 C4 . . . . 0.5(7) no
C1 C2 C3 C4 . . . . -179.2(4) no
C4 C5 C6 C7 . . . . 2.9(8) no
C5 C6 C7 O3 . . . . -176.0(4) no
C5 C6 C7 C2 . . . . -0.8(7) no
C8 O3 C7 C6 . . . . -42.2(6) no
C8 O3 C7 C2 . . . . 142.4(4) no
C3 C2 C7 C6 . . . . -0.9(7) no
C1 C2 C7 C6 . . . . 178.7(4) no
C3 C2 C7 O3 . . . . 174.3(4) no
C1 C2 C7 O3 . . . . -6.0(7) no
C7 O3 C8 C13 . . . . 143.4(4) no
C7 O3 C8 C9 . . . . -41.4(6) no
C13 C8 C9 C10 . . . . 0.4(7) no
O3 C8 C9 C10 . . . . -174.7(4) no
C8 C9 C10 C11 . . . . -0.1(7) no
C8 C9 C10 C14 . . . . 172.5(4) no
O7 C14 C10 C11 . . . . 6.2(6) no
O6 C14 C10 C11 . . . . -174.1(4) no
O7 C14 C10 C9 . . . . -166.3(4) no
O6 C14 C10 C9 . . . . 13.4(6) no
C9 C10 C11 C12 . . . . 0.6(7) no
C14 C10 C11 C12 . . . . -171.9(4) no
C10 C11 C12 C13 . . . . -1.3(7) no
C10 C11 C12 C15 . . . . 178.2(4) no
O3 C8 C13 C12 . . . . 174.3(4) no
C9 C8 C13 C12 . . . . -1.1(7) no
C11 C12 C13 C8 . . . . 1.5(7) no
C15 C12 C13 C8 . . . . -177.9(4) no
Ni2 O4 C15 O5 . . . . 26.9(7) no
Ni2 O4 C15 C12 . . . . -152.1(3) no
C11 C12 C15 O4 . . . . 173.8(4) no
C13 C12 C15 O4 . . . . -6.8(6) no
C11 C12 C15 O5 . . . . -5.3(7) no
C13 C12 C15 O5 . . . . 174.1(4) no
C16 N3 C20 C19 . . . . -1.0(7) no
Ni2 N3 C20 C19 . . . . 178.3(4) no
N3 C20 C19 C18 . . . . 1.6(8) no
C20 C19 C18 C17 . . . . -1.0(8) no
C20 C19 C18 C18 . . . 2_647 178.1(5) no
C19 C18 C17 C16 . . . . 0.0(7) no
C18 C18 C17 C16 2_647 . . . -179.1(5) no
C20 N3 C16 C17 . . . . -0.1(7) no
Ni2 N3 C16 C17 . . . . -179.4(4) no
C18 C17 C16 N3 . . . . 0.6(8) no
C29 N2 C28 C27 . . . . 0.0(8) no
N2 C28 C27 C26 . . . . 0.2(8) no
C28 C27 C26 C30 . . . . -0.3(7) no
C28 C27 C26 C23 . . . . 178.4(5) no
C27 C26 C30 C29 . . . . 0.2(8) no
C23 C26 C30 C29 . . . . -178.5(5) no
C28 N2 C29 C30 . . . . -0.1(9) no
C26 C30 C29 N2 . . . . 0.0(9) no
C27 C26 C23 C22 . . . . -20.7(7) no
C30 C26 C23 C22 . . . . 157.9(5) no
C27 C26 C23 C24 . . . . 158.6(5) no
C30 C26 C23 C24 . . . . -22.7(7) no
C24 C23 C22 C21 . . . . -1.2(8) no
C26 C23 C22 C21 . . . . 178.1(5) no
C25 N1 C21 C22 . . . . 0.7(7) no
Ni1 N1 C21 C22 . . . . -179.2(4) no
C23 C22 C21 N1 . . . . 0.1(8) no
C21 N1 C25 C24 . . . . -0.2(7) no
Ni1 N1 C25 C24 . . . . 179.7(4) no
N1 C25 C24 C23 . . . . -1.0(8) no
C22 C23 C24 C25 . . . . 1.7(7) no
C26 C23 C24 C25 . . . . -177.7(4) no
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_111_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1832425'
loop_
_audit_author_name
_audit_author_address
xuqiwei
;Capital Normal University 
China
;
_audit_update_record             
;
2018-03-26 deposited with the CCDC.	2019-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H22 N2 Ni2 O11'
_chemical_formula_weight         667.89

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.1024(8)
_cell_length_b                   11.5542(9)
_cell_length_c                   12.4520(9)
_cell_angle_alpha                72.963(2)
_cell_angle_beta                 72.622(2)
_cell_angle_gamma                67.195(2)
_cell_volume                     1376.45(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3643
_cell_measurement_theta_min      2.887
_cell_measurement_theta_max      29.872

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.313
_exptl_crystal_size_min          0.122
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             684
_exptl_absorpt_coefficient_mu    1.433
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6773
_exptl_absorpt_correction_T_max  0.8732
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23992
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4836
_reflns_number_gt                4452
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0572P)²+1.3049P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4836
_refine_ls_number_parameters     390
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.53361(3) 0.13482(3) 0.74349(3) 0.02011(12) Uani 1 1 d . . .
Ni2 Ni 0.64364(3) -0.00343(3) 0.99228(3) 0.02126(12) Uani 1 1 d . . .
O8 O 0.48811(17) 0.10002(17) 0.91378(14) 0.0212(4) Uani 1 1 d D . .
O2 O 1.28841(18) -0.16144(19) 0.27637(16) 0.0312(4) Uani 1 1 d . . .
O5 O 0.86422(18) -0.15940(17) 0.56361(14) 0.0270(4) Uani 1 1 d . . .
O6 O 0.64111(18) -0.05627(17) 0.73458(15) 0.0270(4) Uani 1 1 d . . .
O3 O 0.78405(17) -0.10577(19) 0.09448(15) 0.0299(4) Uani 1 1 d . . .
O7 O 0.73581(19) -0.13533(19) 0.88832(16) 0.0312(4) Uani 1 1 d . . .
O9 O 0.55842(19) 0.14176(19) 1.09326(16) 0.0312(4) Uani 1 1 d . . .
H9A H 0.6177 0.1732 1.0911 0.047 Uiso 1 1 d R . .
H9B H 0.5299 0.1092 1.1631 0.047 Uiso 1 1 d R . .
O1 O 1.23019(19) -0.0978(2) 0.10541(15) 0.0337(5) Uani 1 1 d . . .
O4 O 0.63470(18) -0.0998(2) 0.26143(16) 0.0312(4) Uani 1 1 d . . .
N1 N 0.4166(3) 0.3317(2) 0.7262(2) 0.0354(6) Uani 1 1 d . . .
N2 N 0.5476(2) 0.1884(2) 0.56719(19) 0.0271(5) Uani 1 1 d . . .
C14 C 0.8015(3) -0.2649(3) 0.7539(2) 0.0279(6) Uani 1 1 d . . .
C11 C 0.9423(5) -0.5021(3) 0.6914(3) 0.0611(11) Uani 1 1 d . . .
H11 H 0.9881 -0.5812 0.6703 0.073 Uiso 1 1 calc R . .
C26 C 0.2663(6) 0.5292(4) 0.7805(4) 0.0935(19) Uani 1 1 d . . .
H26 H 0.2234 0.5760 0.8385 0.112 Uiso 1 1 calc R . .
C18 C 0.5112(6) 0.2741(4) 0.3432(3) 0.0796(15) Uani 1 1 d U . .
H18 H 0.4994 0.3013 0.2679 0.096 Uiso 1 1 calc R . .
C27 C 0.3525(5) 0.4043(4) 0.8041(3) 0.0675(12) Uani 1 1 d . . .
H27 H 0.3658 0.3699 0.8788 0.081 Uiso 1 1 calc R . .
C19 C 0.4440(4) 0.3566(3) 0.4205(3) 0.0453(8) Uani 1 1 d . . .
C25 C 0.2455(5) 0.5818(4) 0.6732(4) 0.0725(13) Uani 1 1 d . . .
H25 H 0.1873 0.6649 0.6567 0.087 Uiso 1 1 calc R . .
C21 C 0.2982(4) 0.5583(3) 0.4696(3) 0.0547(10) Uani 1 1 d . . .
H21 H 0.2453 0.6426 0.4474 0.066 Uiso 1 1 calc R . .
C20 C 0.3598(4) 0.4843(3) 0.3915(3) 0.0554(10) Uani 1 1 d . . .
H20 H 0.3471 0.5173 0.3166 0.066 Uiso 1 1 calc R . .
C9 C 0.8667(3) -0.2730(3) 0.6401(2) 0.0239(5) Uani 1 1 d . . .
C6 C 0.9071(2) -0.1598(2) 0.4462(2) 0.0221(5) Uani 1 1 d . . .
C3 C 0.9811(2) -0.1307(2) 0.2101(2) 0.0213(5) Uani 1 1 d . . .
H3 H 1.0058 -0.1203 0.1306 0.026 Uiso 1 1 calc R . .
C7 C 1.0320(2) -0.1513(2) 0.3915(2) 0.0223(5) Uani 1 1 d . . .
H7 H 1.0899 -0.1537 0.4334 0.027 Uiso 1 1 calc R . .
C5 C 0.8194(2) -0.1556(2) 0.3860(2) 0.0230(5) Uani 1 1 d . . .
H5 H 0.7368 -0.1645 0.4248 0.028 Uiso 1 1 calc R . .
C15 C 0.7204(2) -0.1405(3) 0.7939(2) 0.0231(5) Uani 1 1 d . . .
C2 C 1.0706(2) -0.1391(2) 0.2724(2) 0.0216(5) Uani 1 1 d . . .
C8 C 0.7503(2) -0.1149(2) 0.2020(2) 0.0221(5) Uani 1 1 d . . .
C1 C 1.2086(2) -0.1324(2) 0.2131(2) 0.0225(5) Uani 1 1 d . . .
C4 C 0.8549(2) -0.1379(2) 0.2667(2) 0.0219(5) Uani 1 1 d . . .
C10 C 0.9364(3) -0.3906(3) 0.6093(3) 0.0387(7) Uani 1 1 d . . .
H10 H 0.9794 -0.3948 0.5333 0.046 Uiso 1 1 calc R . .
C24 C 0.4652(3) 0.3076(3) 0.5330(2) 0.0291(6) Uani 1 1 d . . .
C23 C 0.3959(3) 0.3856(3) 0.6179(3) 0.0313(6) Uani 1 1 d . . .
C12 C 0.8808(5) -0.4963(3) 0.8037(3) 0.0742(15) Uani 1 1 d . . .
H12 H 0.8854 -0.5713 0.8591 0.089 Uiso 1 1 calc R . .
C22 C 0.3116(3) 0.5110(3) 0.5867(3) 0.0461(8) Uani 1 1 d . . .
C16 C 0.6101(4) 0.1146(3) 0.4915(3) 0.0500(9) Uani 1 1 d . . .
H16 H 0.6676 0.0327 0.5142 0.060 Uiso 1 1 calc R . .
C17 C 0.5933(6) 0.1550(4) 0.3776(3) 0.0869(17) Uani 1 1 d U . .
H17 H 0.6384 0.1001 0.3261 0.104 Uiso 1 1 calc R . .
C13 C 0.8121(4) -0.3788(3) 0.8342(3) 0.0555(10) Uani 1 1 d . . .
H13 H 0.7717 -0.3757 0.9108 0.067 Uiso 1 1 calc R . .
O10 O 0.2444(4) -0.2405(5) 0.9489(4) 0.1217(17) Uani 1 1 d GU . .
H10A H 0.2062 -0.2229 1.0151 0.183 Uiso 1 1 d GD . .
H10B H 0.1961 -0.1916 0.9009 0.183 Uiso 1 1 d GD . .
O11 O 1.0038(4) -0.2408(5) 0.9386(4) 0.1282(19) Uani 1 1 d GU . .
H11A H 0.9379 -0.1962 0.9816 0.192 Uiso 1 1 d G . .
H11B H 1.0167 -0.1955 0.8715 0.192 Uiso 1 1 d G . .
H8 H 0.466(3) 0.165(2) 0.941(3) 0.041(10) Uiso 1 1 d D . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O8 1.9828(17) . ?
Ni1 O2 2.0482(18) 2_756 ?
Ni1 N2 2.074(2) . ?
Ni1 O4 2.0801(18) 2_656 ?
Ni1 O6 2.0817(18) . ?
Ni1 N1 2.121(2) . ?
Ni2 O8 2.0222(17) . ?
Ni2 O7 2.0496(18) . ?
Ni2 O1 2.0561(18) 2_756 ?
Ni2 O8 2.0571(17) 2_657 ?
Ni2 O3 2.0790(18) 1_556 ?
Ni2 O9 2.1415(19) . ?
O8 Ni2 2.0571(17) 2_657 ?
O8 H8 0.830(18) . ?
O2 C1 1.245(3) . ?
O2 Ni1 2.0482(18) 2_756 ?
O5 C9 1.373(3) . ?
O5 C6 1.396(3) . ?
O6 C15 1.254(3) . ?
O3 C8 1.262(3) . ?
O3 Ni2 2.0790(18) 1_554 ?
O7 C15 1.258(3) . ?
O9 H9A 0.8570 . ?
O9 H9B 0.8569 . ?
O1 C1 1.259(3) . ?
O1 Ni2 2.0561(18) 2_756 ?
O4 C8 1.249(3) . ?
O4 Ni1 2.0801(18) 2_656 ?
N1 C27 1.324(4) . ?
N1 C23 1.357(4) . ?
N2 C16 1.310(4) . ?
N2 C24 1.352(4) . ?
C14 C13 1.387(4) . ?
C14 C9 1.398(4) . ?
C14 C15 1.508(4) . ?
C11 C12 1.369(5) . ?
C11 C10 1.383(5) . ?
C11 H11 0.9300 . ?
C26 C25 1.345(7) . ?
C26 C27 1.390(6) . ?
C26 H26 0.9300 . ?
C18 C17 1.351(6) . ?
C18 C19 1.395(5) . ?
C18 H18 0.9300 . ?
C27 H27 0.9300 . ?
C19 C24 1.403(4) . ?
C19 C20 1.415(5) . ?
C25 C22 1.395(5) . ?
C25 H25 0.9300 . ?
C21 C20 1.335(6) . ?
C21 C22 1.431(5) . ?
C21 H21 0.9300 . ?
C20 H20 0.9300 . ?
C9 C10 1.380(4) . ?
C6 C5 1.375(4) . ?
C6 C7 1.378(4) . ?
C3 C4 1.390(3) . ?
C3 C2 1.393(3) . ?
C3 H3 0.9300 . ?
C7 C2 1.396(4) . ?
C7 H7 0.9300 . ?
C5 C4 1.392(4) . ?
C5 H5 0.9300 . ?
C2 C1 1.510(3) . ?
C8 C4 1.504(3) . ?
C10 H10 0.9300 . ?
C24 C23 1.434(4) . ?
C23 C22 1.401(4) . ?
C12 C13 1.376(5) . ?
C12 H12 0.9300 . ?
C16 C17 1.403(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C13 H13 0.9300 . ?
O10 H10A 0.8500 . ?
O10 H10B 0.8500 . ?
O11 H11A 0.8500 . ?
O11 H11B 0.8496 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O8 Ni1 O2 97.15(7) . 2_756 ?
O8 Ni1 N2 170.45(8) . . ?
O2 Ni1 N2 90.23(8) 2_756 . ?
O8 Ni1 O4 90.99(7) . 2_656 ?
O2 Ni1 O4 171.01(8) 2_756 2_656 ?
N2 Ni1 O4 82.10(8) . 2_656 ?
O8 Ni1 O6 94.03(7) . . ?
O2 Ni1 O6 87.93(8) 2_756 . ?
N2 Ni1 O6 92.28(8) . . ?
O4 Ni1 O6 87.70(8) 2_656 . ?
O8 Ni1 N1 94.23(8) . . ?
O2 Ni1 N1 95.84(9) 2_756 . ?
N2 Ni1 N1 78.93(9) . . ?
O4 Ni1 N1 87.32(9) 2_656 . ?
O6 Ni1 N1 170.42(9) . . ?
O8 Ni2 O7 96.62(7) . . ?
O8 Ni2 O1 97.02(8) . 2_756 ?
O7 Ni2 O1 89.34(8) . 2_756 ?
O8 Ni2 O8 80.72(7) . 2_657 ?
O7 Ni2 O8 90.88(8) . 2_657 ?
O1 Ni2 O8 177.74(7) 2_756 2_657 ?
O8 Ni2 O3 171.93(7) . 1_556 ?
O7 Ni2 O3 89.64(7) . 1_556 ?
O1 Ni2 O3 88.11(8) 2_756 1_556 ?
O8 Ni2 O3 94.14(7) 2_657 1_556 ?
O8 Ni2 O9 84.21(7) . . ?
O7 Ni2 O9 175.53(8) . . ?
O1 Ni2 O9 86.20(8) 2_756 . ?
O8 Ni2 O9 93.59(7) 2_657 . ?
O3 Ni2 O9 89.94(8) 1_556 . ?
Ni1 O8 Ni2 115.63(8) . . ?
Ni1 O8 Ni2 122.31(9) . 2_657 ?
Ni2 O8 Ni2 99.28(7) . 2_657 ?
Ni1 O8 H8 113(2) . . ?
Ni2 O8 H8 96(2) . . ?
Ni2 O8 H8 106(2) 2_657 . ?
C1 O2 Ni1 134.81(17) . 2_756 ?
C9 O5 C6 119.06(19) . . ?
C15 O6 Ni1 130.69(17) . . ?
C8 O3 Ni2 120.48(16) . 1_554 ?
C15 O7 Ni2 133.31(18) . . ?
Ni2 O9 H9A 109.9 . . ?
Ni2 O9 H9B 109.7 . . ?
H9A O9 H9B 109.0 . . ?
C1 O1 Ni2 125.74(17) . 2_756 ?
C8 O4 Ni1 136.30(18) . 2_656 ?
C27 N1 C23 116.6(3) . . ?
C27 N1 Ni1 130.8(2) . . ?
C23 N1 Ni1 112.25(18) . . ?
C16 N2 C24 118.3(2) . . ?
C16 N2 Ni1 127.2(2) . . ?
C24 N2 Ni1 113.67(18) . . ?
C13 C14 C9 117.5(3) . . ?
C13 C14 C15 118.5(2) . . ?
C9 C14 C15 124.0(2) . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C25 C26 C27 119.5(4) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C17 C18 C19 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
N1 C27 C26 123.7(4) . . ?
N1 C27 H27 118.2 . . ?
C26 C27 H27 118.2 . . ?
C18 C19 C24 116.4(3) . . ?
C18 C19 C20 124.3(3) . . ?
C24 C19 C20 119.3(3) . . ?
C26 C25 C22 119.7(4) . . ?
C26 C25 H25 120.2 . . ?
C22 C25 H25 120.2 . . ?
C20 C21 C22 121.5(3) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C21 C20 C19 121.3(3) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
O5 C9 C10 122.4(2) . . ?
O5 C9 C14 116.7(2) . . ?
C10 C9 C14 120.7(2) . . ?
C5 C6 C7 121.5(2) . . ?
C5 C6 O5 119.3(2) . . ?
C7 C6 O5 118.9(2) . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C6 C7 C2 119.2(2) . . ?
C6 C7 H7 120.4 . . ?
C2 C7 H7 120.4 . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
O6 C15 O7 126.6(2) . . ?
O6 C15 C14 118.1(2) . . ?
O7 C15 C14 115.1(2) . . ?
C3 C2 C7 119.8(2) . . ?
C3 C2 C1 121.2(2) . . ?
C7 C2 C1 119.0(2) . . ?
O4 C8 O3 126.1(2) . . ?
O4 C8 C4 115.2(2) . . ?
O3 C8 C4 118.6(2) . . ?
O2 C1 O1 127.1(2) . . ?
O2 C1 C2 116.3(2) . . ?
O1 C1 C2 116.6(2) . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 C8 121.6(2) . . ?
C5 C4 C8 118.5(2) . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
N2 C24 C19 123.3(3) . . ?
N2 C24 C23 117.3(2) . . ?
C19 C24 C23 119.4(3) . . ?
N1 C23 C22 123.4(3) . . ?
N1 C23 C24 116.9(2) . . ?
C22 C23 C24 119.7(3) . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C25 C22 C23 117.2(3) . . ?
C25 C22 C21 124.2(3) . . ?
C23 C22 C21 118.6(3) . . ?
N2 C16 C17 122.2(3) . . ?
N2 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C18 C17 C16 119.5(4) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C12 C13 C14 121.9(3) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
H10A O10 H10B 109.5 . . ?
H11A O11 H11B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Ni1 O8 Ni2 -37.49(10) 2_756 . . . ?
N2 Ni1 O8 Ni2 -177.8(4) . . . . ?
O4 Ni1 O8 Ni2 138.68(10) 2_656 . . . ?
O6 Ni1 O8 Ni2 50.92(10) . . . . ?
N1 Ni1 O8 Ni2 -133.94(11) . . . . ?
O2 Ni1 O8 Ni2 -158.49(10) 2_756 . . 2_657 ?
N2 Ni1 O8 Ni2 61.2(5) . . . 2_657 ?
O4 Ni1 O8 Ni2 17.68(11) 2_656 . . 2_657 ?
O6 Ni1 O8 Ni2 -70.08(11) . . . 2_657 ?
N1 Ni1 O8 Ni2 105.07(11) . . . 2_657 ?
O7 Ni2 O8 Ni1 -42.96(10) . . . . ?
O1 Ni2 O8 Ni1 47.19(11) 2_756 . . . ?
O8 Ni2 O8 Ni1 -132.77(13) 2_657 . . . ?
O3 Ni2 O8 Ni1 176.4(5) 1_556 . . . ?
O9 Ni2 O8 Ni1 132.62(10) . . . . ?
O7 Ni2 O8 Ni2 89.82(8) . . . 2_657 ?
O1 Ni2 O8 Ni2 179.96(8) 2_756 . . 2_657 ?
O8 Ni2 O8 Ni2 0.0 2_657 . . 2_657 ?
O3 Ni2 O8 Ni2 -50.9(6) 1_556 . . 2_657 ?
O9 Ni2 O8 Ni2 -94.60(8) . . . 2_657 ?
O8 Ni1 O6 C15 -40.2(2) . . . . ?
O2 Ni1 O6 C15 56.8(2) 2_756 . . . ?
N2 Ni1 O6 C15 146.9(2) . . . . ?
O4 Ni1 O6 C15 -131.1(2) 2_656 . . . ?
N1 Ni1 O6 C15 170.2(5) . . . . ?
O8 Ni2 O7 C15 12.5(2) . . . . ?
O1 Ni2 O7 C15 -84.5(2) 2_756 . . . ?
O8 Ni2 O7 C15 93.2(2) 2_657 . . . ?
O3 Ni2 O7 C15 -172.6(2) 1_556 . . . ?
O9 Ni2 O7 C15 -88.0(10) . . . . ?
O8 Ni1 N1 C27 7.7(4) . . . . ?
O2 Ni1 N1 C27 -89.9(4) 2_756 . . . ?
N2 Ni1 N1 C27 -179.0(4) . . . . ?
O4 Ni1 N1 C27 98.5(4) 2_656 . . . ?
O6 Ni1 N1 C27 157.2(5) . . . . ?
O8 Ni1 N1 C23 -165.2(2) . . . . ?
O2 Ni1 N1 C23 97.1(2) 2_756 . . . ?
N2 Ni1 N1 C23 8.0(2) . . . . ?
O4 Ni1 N1 C23 -74.4(2) 2_656 . . . ?
O6 Ni1 N1 C23 -15.7(7) . . . . ?
O8 Ni1 N2 C16 -133.3(5) . . . . ?
O2 Ni1 N2 C16 86.0(3) 2_756 . . . ?
O4 Ni1 N2 C16 -89.3(3) 2_656 . . . ?
O6 Ni1 N2 C16 -1.9(3) . . . . ?
N1 Ni1 N2 C16 -178.1(3) . . . . ?
O8 Ni1 N2 C24 35.9(6) . . . . ?
O2 Ni1 N2 C24 -104.84(19) 2_756 . . . ?
O4 Ni1 N2 C24 79.87(19) 2_656 . . . ?
O6 Ni1 N2 C24 167.23(19) . . . . ?
N1 Ni1 N2 C24 -8.93(19) . . . . ?
C23 N1 C27 C26 0.7(7) . . . . ?
Ni1 N1 C27 C26 -172.0(4) . . . . ?
C25 C26 C27 N1 -0.3(9) . . . . ?
C17 C18 C19 C24 -1.1(7) . . . . ?
C17 C18 C19 C20 177.7(5) . . . . ?
C27 C26 C25 C22 -0.7(9) . . . . ?
C22 C21 C20 C19 -1.7(6) . . . . ?
C18 C19 C20 C21 179.9(4) . . . . ?
C24 C19 C20 C21 -1.3(6) . . . . ?
C6 O5 C9 C10 14.8(4) . . . . ?
C6 O5 C9 C14 -169.1(2) . . . . ?
C13 C14 C9 O5 -174.9(3) . . . . ?
C15 C14 C9 O5 5.4(4) . . . . ?
C13 C14 C9 C10 1.3(5) . . . . ?
C15 C14 C9 C10 -178.4(3) . . . . ?
C9 O5 C6 C5 83.6(3) . . . . ?
C9 O5 C6 C7 -102.9(3) . . . . ?
C5 C6 C7 C2 -0.5(4) . . . . ?
O5 C6 C7 C2 -173.9(2) . . . . ?
C7 C6 C5 C4 -2.3(4) . . . . ?
O5 C6 C5 C4 171.1(2) . . . . ?
Ni1 O6 C15 O7 14.1(4) . . . . ?
Ni1 O6 C15 C14 -169.67(17) . . . . ?
Ni2 O7 C15 O6 2.9(4) . . . . ?
Ni2 O7 C15 C14 -173.35(18) . . . . ?
C13 C14 C15 O6 -135.2(3) . . . . ?
C9 C14 C15 O6 44.4(4) . . . . ?
C13 C14 C15 O7 41.4(4) . . . . ?
C9 C14 C15 O7 -138.9(3) . . . . ?
C4 C3 C2 C7 -1.7(4) . . . . ?
C4 C3 C2 C1 179.6(2) . . . . ?
C6 C7 C2 C3 2.5(4) . . . . ?
C6 C7 C2 C1 -178.8(2) . . . . ?
Ni1 O4 C8 O3 33.6(4) 2_656 . . . ?
Ni1 O4 C8 C4 -150.37(19) 2_656 . . . ?
Ni2 O3 C8 O4 21.4(4) 1_554 . . . ?
Ni2 O3 C8 C4 -154.51(18) 1_554 . . . ?
Ni1 O2 C1 O1 16.0(4) 2_756 . . . ?
Ni1 O2 C1 C2 -163.70(18) 2_756 . . . ?
Ni2 O1 C1 O2 -31.7(4) 2_756 . . . ?
Ni2 O1 C1 C2 148.08(18) 2_756 . . . ?
C3 C2 C1 O2 -168.7(2) . . . . ?
C7 C2 C1 O2 12.6(4) . . . . ?
C3 C2 C1 O1 11.5(4) . . . . ?
C7 C2 C1 O1 -167.2(2) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C2 C3 C4 C8 173.2(2) . . . . ?
C6 C5 C4 C3 3.0(4) . . . . ?
C6 C5 C4 C8 -171.4(2) . . . . ?
O4 C8 C4 C3 -166.9(2) . . . . ?
O3 C8 C4 C3 9.5(4) . . . . ?
O4 C8 C4 C5 7.5(4) . . . . ?
O3 C8 C4 C5 -176.2(2) . . . . ?
O5 C9 C10 C11 176.0(3) . . . . ?
C14 C9 C10 C11 0.0(5) . . . . ?
C12 C11 C10 C9 -1.0(7) . . . . ?
C16 N2 C24 C19 -0.4(4) . . . . ?
Ni1 N2 C24 C19 -170.6(2) . . . . ?
C16 N2 C24 C23 178.8(3) . . . . ?
Ni1 N2 C24 C23 8.6(3) . . . . ?
C18 C19 C24 N2 1.3(5) . . . . ?
C20 C19 C24 N2 -177.6(3) . . . . ?
C18 C19 C24 C23 -178.0(4) . . . . ?
C20 C19 C24 C23 3.2(5) . . . . ?
C27 N1 C23 C22 -0.3(5) . . . . ?
Ni1 N1 C23 C22 173.8(2) . . . . ?
C27 N1 C23 C24 179.9(3) . . . . ?
Ni1 N1 C23 C24 -6.1(3) . . . . ?
N2 C24 C23 N1 -1.6(4) . . . . ?
C19 C24 C23 N1 177.7(3) . . . . ?
N2 C24 C23 C22 178.6(3) . . . . ?
C19 C24 C23 C22 -2.2(4) . . . . ?
C10 C11 C12 C13 0.6(8) . . . . ?
C26 C25 C22 C23 1.1(7) . . . . ?
C26 C25 C22 C21 -179.0(5) . . . . ?
N1 C23 C22 C25 -0.7(5) . . . . ?
C24 C23 C22 C25 179.2(3) . . . . ?
N1 C23 C22 C21 179.5(3) . . . . ?
C24 C23 C22 C21 -0.6(5) . . . . ?
C20 C21 C22 C25 -177.2(4) . . . . ?
C20 C21 C22 C23 2.6(6) . . . . ?
C24 N2 C16 C17 -0.6(6) . . . . ?
Ni1 N2 C16 C17 168.1(4) . . . . ?
C19 C18 C17 C16 0.2(9) . . . . ?
N2 C16 C17 C18 0.7(8) . . . . ?
C11 C12 C13 C14 0.8(8) . . . . ?
C9 C14 C13 C12 -1.8(6) . . . . ?
C15 C14 C13 C12 177.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.670
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.083
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_111_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1832419'
loop_
_audit_author_name
_audit_author_address
xuqiwei
;Capital Normal University 
China
;
_audit_update_record             
;
2018-03-26 deposited with the CCDC.	2019-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H30 Cu3 N4 O14'
_chemical_formula_weight         1101.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0683(8)
_cell_length_b                   10.8967(9)
_cell_length_c                   11.0913(9)
_cell_angle_alpha                89.393(3)
_cell_angle_beta                 85.366(2)
_cell_angle_gamma                64.932(2)
_cell_volume                     1098.24(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7279
_cell_measurement_theta_min      3.042
_cell_measurement_theta_max      26.080

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.268
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.054
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             557
_exptl_absorpt_coefficient_mu    1.518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7028
_exptl_absorpt_correction_T_max  0.8882
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19635
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_sigmaI/netI    0.0496
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3866
_reflns_number_gt                3074
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0541P)²+0.4313P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3866
_refine_ls_number_parameters     322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0919
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.33416(4) 0.28607(4) 0.13954(3) 0.02181(14) Uani 1 1 d . . .
Cu2 Cu 0.5000 0.5000 0.0000 0.02709(17) Uani 1 2 d S . .
O7 O 0.5536(2) 0.1981(2) 0.12496(19) 0.0286(5) Uani 1 1 d . . .
O5 O 1.1334(2) 0.2851(2) 0.15042(19) 0.0270(5) Uani 1 1 d . . .
O6 O 0.6324(3) 0.3587(3) 0.0918(3) 0.0540(8) Uani 1 1 d . . .
O3 O 1.0128(3) -0.2037(2) 0.2290(2) 0.0390(6) Uani 1 1 d . . .
O1 O 1.4122(3) -0.3921(3) 0.1477(2) 0.0511(7) Uani 1 1 d . . .
O2 O 1.2566(3) -0.4874(2) 0.1486(2) 0.0382(6) Uani 1 1 d . . .
O4 O 1.3041(2) 0.0749(2) 0.1507(2) 0.0426(7) Uani 1 1 d . . .
N1 N 0.3290(3) 0.2920(3) -0.0397(2) 0.0243(6) Uani 1 1 d . . .
N2 N 0.3328(3) 0.2828(3) -0.6768(2) 0.0288(6) Uani 1 1 d . . .
C18 C 0.3209(3) 0.2872(3) -0.2899(3) 0.0271(7) Uani 1 1 d . . .
C23 C 0.4521(4) 0.2114(4) -0.6190(3) 0.0449(10) Uani 1 1 d . . .
H23 H 0.5397 0.1598 -0.6646 0.054 Uiso 1 1 calc R . .
C6 C 1.0357(5) -0.1845(4) 0.4418(4) 0.0519(11) Uani 1 1 d . . .
H6 H 0.9407 -0.1158 0.4507 0.062 Uiso 1 1 calc R . .
C1 C 1.3056(4) -0.4136(3) 0.1940(3) 0.0316(8) Uani 1 1 d . . .
C4 C 1.2548(6) -0.3264(5) 0.5281(4) 0.0639(13) Uani 1 1 d . . .
H4 H 1.3081 -0.3566 0.5955 0.077 Uiso 1 1 calc R . .
C3 C 1.3165(5) -0.3836(4) 0.4152(4) 0.0511(11) Uani 1 1 d . . .
H3 H 1.4132 -0.4493 0.4066 0.061 Uiso 1 1 calc R . .
C5 C 1.1166(6) -0.2263(5) 0.5403(4) 0.0681(14) Uani 1 1 d . . .
H5 H 1.0762 -0.1856 0.6159 0.082 Uiso 1 1 calc R . .
C15 C 0.6512(3) 0.2414(3) 0.1147(3) 0.0279(8) Uani 1 1 d . . .
C10 C 0.8054(3) 0.1445(3) 0.1376(3) 0.0232(7) Uani 1 1 d . . .
C8 C 0.9815(3) -0.0712(3) 0.1953(3) 0.0279(8) Uani 1 1 d . . .
C12 C 1.0562(3) 0.1067(3) 0.1538(3) 0.0239(7) Uani 1 1 d . . .
C24 C 0.2091(4) 0.3532(4) -0.6090(3) 0.0416(10) Uani 1 1 d . . .
H24 H 0.1245 0.4033 -0.6474 0.050 Uiso 1 1 calc R . .
C16 C 0.4248(4) 0.1867(3) -0.1072(3) 0.0295(8) Uani 1 1 d . . .
H16 H 0.4948 0.1144 -0.0693 0.035 Uiso 1 1 calc R . .
C11 C 0.9135(3) 0.1923(3) 0.1300(3) 0.0242(7) Uani 1 1 d . . .
H11 H 0.8903 0.2815 0.1091 0.029 Uiso 1 1 calc R . .
C17 C 0.4244(4) 0.1808(3) -0.2307(3) 0.0310(8) Uani 1 1 d . . .
H17 H 0.4934 0.1056 -0.2748 0.037 Uiso 1 1 calc R . .
C13 C 1.0902(3) -0.0254(3) 0.1850(3) 0.0293(8) Uani 1 1 d . . .
H13 H 1.1863 -0.0835 0.1992 0.035 Uiso 1 1 calc R . .
C14 C 1.1738(3) 0.1581(3) 0.1514(3) 0.0253(7) Uani 1 1 d . . .
C9 C 0.8395(3) 0.0120(3) 0.1701(3) 0.0270(7) Uani 1 1 d . . .
H9 H 0.7674 -0.0204 0.1748 0.032 Uiso 1 1 calc R . .
C21 C 0.3229(4) 0.2843(3) -0.4236(3) 0.0294(8) Uani 1 1 d . . .
C20 C 0.2269(4) 0.3938(3) -0.0947(3) 0.0327(8) Uani 1 1 d . . .
H20 H 0.1578 0.4666 -0.0480 0.039 Uiso 1 1 calc R . .
C25 C 0.1998(4) 0.3558(4) -0.4848(3) 0.0414(10) Uani 1 1 d . . .
H25 H 0.1099 0.4060 -0.4415 0.050 Uiso 1 1 calc R . .
C19 C 0.2206(4) 0.3946(4) -0.2182(3) 0.0355(9) Uani 1 1 d . . .
H19 H 0.1485 0.4678 -0.2536 0.043 Uiso 1 1 calc R . .
C7 C 1.0953(4) -0.2445(3) 0.3296(3) 0.0320(8) Uani 1 1 d . . .
C2 C 1.2370(4) -0.3452(3) 0.3144(3) 0.0296(8) Uani 1 1 d . . .
C22 C 0.4515(4) 0.2106(4) -0.4954(3) 0.0497(11) Uani 1 1 d . . .
H22 H 0.5379 0.1603 -0.4594 0.060 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.993(2) . ?
Cu1 O7 1.995(2) . ?
Cu1 O5 2.020(2) 1_455 ?
Cu1 N2 2.036(3) 1_556 ?
Cu1 O2 2.252(2) 1_465 ?
Cu1 C14 2.538(3) 1_455 ?
Cu2 O6 1.906(2) 2_665 ?
Cu2 O6 1.906(2) . ?
Cu2 O1 1.943(3) 1_465 ?
Cu2 O1 1.943(3) 2_755 ?
O7 C15 1.254(4) . ?
O5 C14 1.266(4) . ?
O5 Cu1 2.020(2) 1_655 ?
O6 C15 1.238(4) . ?
O3 C8 1.395(4) . ?
O3 C7 1.400(4) . ?
O1 C1 1.261(4) . ?
O1 Cu2 1.943(3) 1_645 ?
O2 C1 1.236(4) . ?
O2 Cu1 2.252(2) 1_645 ?
O4 C14 1.239(4) . ?
N1 C16 1.331(4) . ?
N1 C20 1.334(4) . ?
N2 C24 1.325(4) . ?
N2 C23 1.335(4) . ?
N2 Cu1 2.036(3) 1_554 ?
C18 C19 1.383(5) . ?
C18 C17 1.390(4) . ?
C18 C21 1.482(4) . ?
C23 C22 1.370(5) . ?
C23 H23 0.9300 . ?
C6 C5 1.373(6) . ?
C6 C7 1.378(5) . ?
C6 H6 0.9300 . ?
C1 C2 1.501(5) . ?
C4 C5 1.353(6) . ?
C4 C3 1.381(6) . ?
C4 H4 0.9300 . ?
C3 C2 1.384(5) . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
C15 C10 1.503(4) . ?
C10 C9 1.386(4) . ?
C10 C11 1.388(4) . ?
C8 C13 1.378(4) . ?
C8 C9 1.381(4) . ?
C12 C13 1.379(4) . ?
C12 C11 1.387(4) . ?
C12 C14 1.507(4) . ?
C24 C25 1.373(5) . ?
C24 H24 0.9300 . ?
C16 C17 1.372(4) . ?
C16 H16 0.9300 . ?
C11 H11 0.9300 . ?
C17 H17 0.9300 . ?
C13 H13 0.9300 . ?
C14 Cu1 2.538(3) 1_655 ?
C9 H9 0.9300 . ?
C21 C25 1.382(5) . ?
C21 C22 1.386(5) . ?
C20 C19 1.376(4) . ?
C20 H20 0.9300 . ?
C25 H25 0.9300 . ?
C19 H19 0.9300 . ?
C7 C2 1.381(5) . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 O7 91.55(9) . . ?
N1 Cu1 O5 88.09(9) . 1_455 ?
O7 Cu1 O5 153.92(9) . 1_455 ?
N1 Cu1 N2 178.32(10) . 1_556 ?
O7 Cu1 N2 90.13(10) . 1_556 ?
O5 Cu1 N2 90.41(9) 1_455 1_556 ?
N1 Cu1 O2 90.04(10) . 1_465 ?
O7 Cu1 O2 108.92(9) . 1_465 ?
O5 Cu1 O2 97.16(9) 1_455 1_465 ?
N2 Cu1 O2 89.38(10) 1_556 1_465 ?
N1 Cu1 C14 89.91(10) . 1_455 ?
O7 Cu1 C14 124.37(10) . 1_455 ?
O5 Cu1 C14 29.57(9) 1_455 1_455 ?
N2 Cu1 C14 89.17(10) 1_556 1_455 ?
O2 Cu1 C14 126.69(10) 1_465 1_455 ?
O6 Cu2 O6 180.00(19) 2_665 . ?
O6 Cu2 O1 90.16(13) 2_665 1_465 ?
O6 Cu2 O1 89.84(13) . 1_465 ?
O6 Cu2 O1 89.84(13) 2_665 2_755 ?
O6 Cu2 O1 90.16(13) . 2_755 ?
O1 Cu2 O1 180.00(16) 1_465 2_755 ?
C15 O7 Cu1 134.3(2) . . ?
C14 O5 Cu1 98.51(18) . 1_655 ?
C15 O6 Cu2 134.7(2) . . ?
C8 O3 C7 113.8(2) . . ?
C1 O1 Cu2 111.3(2) . 1_645 ?
C1 O2 Cu1 132.6(2) . 1_645 ?
C16 N1 C20 118.3(3) . . ?
C16 N1 Cu1 119.1(2) . . ?
C20 N1 Cu1 122.5(2) . . ?
C24 N2 C23 116.9(3) . . ?
C24 N2 Cu1 119.9(2) . 1_554 ?
C23 N2 Cu1 123.1(2) . 1_554 ?
C19 C18 C17 116.7(3) . . ?
C19 C18 C21 122.8(3) . . ?
C17 C18 C21 120.5(3) . . ?
N2 C23 C22 123.1(3) . . ?
N2 C23 H23 118.5 . . ?
C22 C23 H23 118.5 . . ?
C5 C6 C7 120.0(4) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
O2 C1 O1 125.0(3) . . ?
O2 C1 C2 118.7(3) . . ?
O1 C1 C2 116.3(3) . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C4 C5 C6 120.4(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
O6 C15 O7 126.3(3) . . ?
O6 C15 C10 115.8(3) . . ?
O7 C15 C10 117.8(3) . . ?
C9 C10 C11 120.2(3) . . ?
C9 C10 C15 121.5(3) . . ?
C11 C10 C15 118.3(3) . . ?
C13 C8 C9 120.9(3) . . ?
C13 C8 O3 120.9(3) . . ?
C9 C8 O3 118.2(3) . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 C14 119.3(3) . . ?
C11 C12 C14 120.7(3) . . ?
N2 C24 C25 123.2(3) . . ?
N2 C24 H24 118.4 . . ?
C25 C24 H24 118.4 . . ?
N1 C16 C17 122.5(3) . . ?
N1 C16 H16 118.7 . . ?
C17 C16 H16 118.7 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C16 C17 C18 120.0(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C8 C13 C12 119.9(3) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
O4 C14 O5 123.4(3) . . ?
O4 C14 C12 118.8(3) . . ?
O5 C14 C12 117.8(3) . . ?
O4 C14 Cu1 71.52(18) . 1_655 ?
O5 C14 Cu1 51.92(15) . 1_655 ?
C12 C14 Cu1 169.5(2) . 1_655 ?
C8 C9 C10 119.2(3) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C25 C21 C22 115.8(3) . . ?
C25 C21 C18 123.0(3) . . ?
C22 C21 C18 121.2(3) . . ?
N1 C20 C19 122.2(3) . . ?
N1 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?
C24 C25 C21 120.5(3) . . ?
C24 C25 H25 119.7 . . ?
C21 C25 H25 119.7 . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C6 C7 C2 120.7(3) . . ?
C6 C7 O3 120.3(3) . . ?
C2 C7 O3 118.9(3) . . ?
C7 C2 C3 117.9(3) . . ?
C7 C2 C1 122.4(3) . . ?
C3 C2 C1 119.7(3) . . ?
C23 C22 C21 120.5(3) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu1 O7 C15 86.7(3) . . . . ?
O5 Cu1 O7 C15 175.5(3) 1_455 . . . ?
N2 Cu1 O7 C15 -93.3(3) 1_556 . . . ?
O2 Cu1 O7 C15 -3.9(3) 1_465 . . . ?
C14 Cu1 O7 C15 177.7(3) 1_455 . . . ?
O6 Cu2 O6 C15 17(100) 2_665 . . . ?
O1 Cu2 O6 C15 114.1(4) 1_465 . . . ?
O1 Cu2 O6 C15 -65.9(4) 2_755 . . . ?
O7 Cu1 N1 C16 39.7(2) . . . . ?
O5 Cu1 N1 C16 -114.2(2) 1_455 . . . ?
N2 Cu1 N1 C16 -141(3) 1_556 . . . ?
O2 Cu1 N1 C16 148.6(2) 1_465 . . . ?
C14 Cu1 N1 C16 -84.7(2) 1_455 . . . ?
O7 Cu1 N1 C20 -144.8(3) . . . . ?
O5 Cu1 N1 C20 61.3(3) 1_455 . . . ?
N2 Cu1 N1 C20 34(4) 1_556 . . . ?
O2 Cu1 N1 C20 -35.8(3) 1_465 . . . ?
C14 Cu1 N1 C20 90.9(3) 1_455 . . . ?
C24 N2 C23 C22 -1.3(6) . . . . ?
Cu1 N2 C23 C22 179.2(3) 1_554 . . . ?
Cu1 O2 C1 O1 78.5(5) 1_645 . . . ?
Cu1 O2 C1 C2 -100.3(3) 1_645 . . . ?
Cu2 O1 C1 O2 -4.0(4) 1_645 . . . ?
Cu2 O1 C1 C2 174.8(2) 1_645 . . . ?
C5 C4 C3 C2 -3.2(7) . . . . ?
C3 C4 C5 C6 2.2(8) . . . . ?
C7 C6 C5 C4 -0.1(7) . . . . ?
Cu2 O6 C15 O7 -31.8(6) . . . . ?
Cu2 O6 C15 C10 151.2(3) . . . . ?
Cu1 O7 C15 O6 -12.2(5) . . . . ?
Cu1 O7 C15 C10 164.8(2) . . . . ?
O6 C15 C10 C9 176.7(3) . . . . ?
O7 C15 C10 C9 -0.6(5) . . . . ?
O6 C15 C10 C11 -0.8(4) . . . . ?
O7 C15 C10 C11 -178.1(3) . . . . ?
C7 O3 C8 C13 47.4(4) . . . . ?
C7 O3 C8 C9 -134.0(3) . . . . ?
C23 N2 C24 C25 0.4(6) . . . . ?
Cu1 N2 C24 C25 179.9(3) 1_554 . . . ?
C20 N1 C16 C17 1.5(5) . . . . ?
Cu1 N1 C16 C17 177.3(3) . . . . ?
C13 C12 C11 C10 -0.1(5) . . . . ?
C14 C12 C11 C10 -177.4(3) . . . . ?
C9 C10 C11 C12 0.7(5) . . . . ?
C15 C10 C11 C12 178.3(3) . . . . ?
N1 C16 C17 C18 -0.2(5) . . . . ?
C19 C18 C17 C16 -0.9(5) . . . . ?
C21 C18 C17 C16 177.6(3) . . . . ?
C9 C8 C13 C12 2.6(5) . . . . ?
O3 C8 C13 C12 -178.8(3) . . . . ?
C11 C12 C13 C8 -1.5(5) . . . . ?
C14 C12 C13 C8 175.8(3) . . . . ?
Cu1 O5 C14 O4 2.6(4) 1_655 . . . ?
Cu1 O5 C14 C12 -177.5(2) 1_655 . . . ?
C13 C12 C14 O4 15.9(5) . . . . ?
C11 C12 C14 O4 -166.8(3) . . . . ?
C13 C12 C14 O5 -163.9(3) . . . . ?
C11 C12 C14 O5 13.4(5) . . . . ?
C13 C12 C14 Cu1 -174.7(11) . . . 1_655 ?
C11 C12 C14 Cu1 2.6(14) . . . 1_655 ?
C13 C8 C9 C10 -2.0(5) . . . . ?
O3 C8 C9 C10 179.4(3) . . . . ?
C11 C10 C9 C8 0.3(5) . . . . ?
C15 C10 C9 C8 -177.2(3) . . . . ?
C19 C18 C21 C25 -25.8(5) . . . . ?
C17 C18 C21 C25 155.8(4) . . . . ?
C19 C18 C21 C22 152.8(4) . . . . ?
C17 C18 C21 C22 -25.6(5) . . . . ?
C16 N1 C20 C19 -1.8(5) . . . . ?
Cu1 N1 C20 C19 -177.4(3) . . . . ?
N2 C24 C25 C21 0.8(6) . . . . ?
C22 C21 C25 C24 -1.0(6) . . . . ?
C18 C21 C25 C24 177.7(3) . . . . ?
N1 C20 C19 C18 0.7(5) . . . . ?
C17 C18 C19 C20 0.6(5) . . . . ?
C21 C18 C19 C20 -177.8(3) . . . . ?
C5 C6 C7 C2 -1.0(6) . . . . ?
C5 C6 C7 O3 179.1(4) . . . . ?
C8 O3 C7 C6 66.4(4) . . . . ?
C8 O3 C7 C2 -113.4(3) . . . . ?
C6 C7 C2 C3 0.1(5) . . . . ?
O3 C7 C2 C3 179.9(3) . . . . ?
C6 C7 C2 C1 179.6(3) . . . . ?
O3 C7 C2 C1 -0.6(5) . . . . ?
C4 C3 C2 C7 2.0(6) . . . . ?
C4 C3 C2 C1 -177.5(4) . . . . ?
O2 C1 C2 C7 -67.8(4) . . . . ?
O1 C1 C2 C7 113.3(4) . . . . ?
O2 C1 C2 C3 111.7(4) . . . . ?
O1 C1 C2 C3 -67.2(5) . . . . ?
N2 C23 C22 C21 1.0(7) . . . . ?
C25 C21 C22 C23 0.1(6) . . . . ?
C18 C21 C22 C23 -178.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.084
